10 days in Detroit, Chicago & Milwaukee Itinerary

Founded in 1701 by a French explorer and adventurer, Detroit exerted a profound impact on the world for most of the 20th century.

Your day by day itinerary now includes Antique Touring Company, The Ford Piquette Avenue Plant, Holocaust Memorial Center, and other attractions you added. On the 30th (Thu), steep yourself in history at Motown Museum. Here are some ideas for day two: take an in-depth tour of Holocaust Memorial Center, then steep yourself in history at The Ford Piquette Avenue Plant, then squeeze the most out of the city with Antique Touring Company, and finally see where the action happens at Comerica Park.

To find where to stay, photos, other places to visit, and other tourist information, you can read our Detroit online tour itinerary maker.

Ashburn to Detroit is an approximately 4.5-hour combination of car and flight. You can also drive. When traveling from Ashburn in June, plan for little chillier days and about the same nights in Detroit: temperatures range from 79°F by day to 61°F at night. Wrap up your sightseeing on the 2nd (Sat) to allow time to fly to Chicago.

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.

Your day by day itinerary now includes Navy Pier, Chicago Crime Tours and Experiences and Wrigley Field. There's still lots to do: explore the world behind art at The Art Institute of Chicago, take in panoramic vistas at 360 Chicago Observation Deck, walk around Millennium Park, and get up close and personal with brilliant marine life at Shedd Aquarium.

To see reviews, maps, traveler tips, and other tourist information, you can read our Chicago online visit planner.

You can fly from Detroit to Chicago in 3 hours. Alternatively, you can drive; or take a train. The time zone difference when traveling from Detroit to Chicago is minus 1 hour. In July in Chicago, expect temperatures between 83°F during the day and 67°F at night. Wrap up your sightseeing on the 7th (Thu) to allow time to drive to Milwaukee.

Milwaukee boasts well-preserved historical districts with a rich European past and a strong beer-brewing tradition.

Your day by day itinerary now includes Miller Brewery Tour as well as Harley-Davidson Museum. Start off your visit on the 8th (Fri): see the interesting displays at Harley-Davidson Museum and then indulge your thirst for a good beer at Miller Brewery Tour.

To see where to stay, more things to do, other places to visit, and tourist information, you can read our Milwaukee tour builder website.

Drive from Chicago to Milwaukee in 1.5 hours. Alternatively, you can take a train; or take a bus. In July in Milwaukee, expect temperatures between 80°F during the day and 63°F at night. Finish your sightseeing early on the 9th (Sat) to allow enough time to travel back home.